“AS IF! ” Those two little words, italicized and paired with a perfectly plucked brow furrow, were all it took for Alicia Silverstone to forever cement her status as a ’90s icon. It was the summer of 1995, and multiplexes were grunting with the testosterone of blockbusters like Batman Forever, Apollo 13, and Under Siege 2: Dark Territory. Writer-director Amy Heckerling was best known for her sex-addled comedy, Fast Times at Ridgemont High, and Silverstone, then 18, had achieved modest fame for her turn as a deranged teenager in The Crush, and by appearing in a trilogy of Aerosmith videos with Liv Tyler.

Clueless, Heckerling’s Beverly Hills High School–set reimagining of Jane Austen’s Emma, became a sleeper hit and turned Silverstone, who played the ultimate Valley Girl Cher Horowitz, into an overnight star. Shortly thereafter, the young actor signed a $10 million, multipicture deal with Columbia- TriStar and started her own production company. She named it, appropriately, First Kiss Productions, and two years later it produced its only film, Excess Baggage. Silverstone went on to appear primarily in romantic comedies (Blast from the Past, Beauty Shop) and franchise films (Batman & Robin, Scooby Doo 2: Monsters Unleashed). Heckerling followed up Clueless five years later with Loser and, seven years after that, I Could Never Be Your Woman, which, due to a money-related fallout, was released straight-to-DVD.

Silverstone, who continues to steadily work in theater, began to pursue her twin passions for environmentalism and animal rights. In 2009, she released a New York Times best-selling guide to vegan living called The Kind Diet, which led to The Kind Life, an offshoot website and a less smug version of Gwyneth Paltrow’s GOOP, and, most recently, a green cosmetics line for Juice Beauty. She also married musician, radio host, and fellow vegan Christopher Jarecki, with whom she had a baby boy, Bear Blu, last year.

Now 35, the onetime queen of Valspeak has reentered Hollywood through the back door, appearing on critically acclaimed television series (Suburgatory and Childrens Hospital) and in festival-friendly films (The Art of Getting By and this fall’s Butter, an ensemble comedy centered on a butter-sculpting competition). But it’s her reunion with Heckerling this October in Vamps that has people, like, totally buggin’. As Goody, Silverstone swans about New York City with her socialite best friend Stacey (Krysten Ritter), until they fall in love with two mortals and are forced to choose between eros and life everlasting.

In anticipation of the film’s release, we brought Silverstone and Heckerling together, and asked them to take us back—all the way back to the very first time they met.

ALICIA SILVERSTONE: We met at this fancy-ish restaurant in Beverly Hills called Maple Drive. My agent told me that I’d be meeting an amazing director who’d done Fast Times at Ridgemont High. I was 17, so I didn’t really know what that meant, other than that it seemed important.AMY HECKERLING: I’d seen your Aerosmith videos. The first one was “Cryin’,” where you’re mad at the guy and then someone steals your purse and then you do the bungee jumping. I’m always on the treadmill watching videos starring millions of supposedly hot girls. But I responded to you. You had personality and a soul. When I was writing the script for Clueless, I had a vague notion in my head of Cher as a pretty, sweet blonde, who, in spite of being the American ideal, people still really like. You had that marilyn monroe thing, which is that other women love you, too. I’m always so happy to see you in things. I saw the play—what was it? Time and Again?

Time Stands Still.And I saw you in the mamet play [Speed-the-Plow] and the Shakespeare movie [Love’s Labour’s Lost], and the one where you meet what’s-his-name in the fallout shelter…

Blast from the Past.Yeah, Blast from the Past!

You were always so hip. You always knew what was going on with young people much more than I did, and I was supposed to be the young person. I even went to the Clueless school, Beverly Hills High, for a semester, but you noticed all these things that I didn’t. When we worked together on Vamps all these years later, I felt very connected to you. Maybe it’s because I’m a woman now, too.There are a few people in my life who I’ve watched grow up. The nature of our relationship has changed, of course, but the feeling that I need to protect you didn’t go away.

There are so many things I would have done differently after Clueless, but I think we all have that period in our lives where we think, if I could just press the restart button!You went through the biggest, craziest upheaval. But that’s what happens when you take someone who’s 17, and start telling her that all of these millions of dollars are dependent on her. There was a headline on the cover of a magazine back then that said, “Can Alicia Silverstone Save Sony?” What the hell? I always thought you should be reading the classics and going on dates. It was just crazy, the weight that was put onto you.

I can’t tell you that if I went back in time, as that little girl, I wouldn’t have made the same choices.
But they were decisions that a lot of people around you were making: studio heads and management. It’s hideous the way people hang on—and suck from—talent. It’s the kind of stuff that makes a lot of people go crazy.